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Synthesis of 2,5-dilithio-1-methylimidazole

✍ Scribed by Gideon Shapiro; Martin Marzi

Book ID: 104215811
Publisher: Elsevier Science
Year: 1993
Tongue: French
Weight: 290 KB
Volume: 34
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79166-0

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✦ Synopsis

C5 to C2 position migratiw of 2-trialkylsilyl and thiophctgd groups have bus observed upon lithhth at the Cs-position of cxxqwkg C2-subwituted l-muhylixnkko~. Double brominelithium exchange of I-mcthyL2$sle (5) affords a facile, qluwthive and uuequivocal synthc& of 2,5_dilithio_l~l-~~ (4). Raction of 4 with ol~t equivaknt of DMP occurs selectively at the cs position to give I-methylimKkolc-5caliJoxaahyde (1). In the purse of our synthesis of (+)-pilosininc we became ilaracd ill akznative routes for the important starthg mat&al, I-methyl-inlidazole-s-carboxcarboxaldehyde (1). Qassically, 1 is lnqarcd by a five step procedure starting fbm sarcosine methylester? Man tecuuly the practical umvcrsia of 5-bromo-l-mcthylimidazole(2)to1intwostel#pvia~reactionhasbeen~~Thereare~~~,~~to bothmaods.4

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